149451-80-9

Basic information

• Product Name: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE
• Synonyms: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE
• CAS NO: 149451-80-9
• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.35
• Mol File: 149451-80-9.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE(149451-80-9)
• EPA Substance Registry System: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE(149451-80-9)

Safety Data

• Hazardous Substances Data: 149451-80-9(Hazardous Substances Data)

Upstream product

• 103127-52-2 ((S)-1-benzylallyl)carbamic acid tert-butyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 1393955-00-4 (3S)-3-([(1,1-dimethylethyl)oxy]carbonylamino)-1-(methylsulfanyl)-2-oxo-4-phenylbutyl ethanoate 
• 1393955-13-9 (3S)-3-([(1,1-dimethylethyl)oxy]carbonylamino)-2-hydroxy-4-phenylbutyl ethanoate 
• 1268240-91-0 (S)-N-((S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylethyl)-2-methylpropane-2-sulfinamide 
• 1202649-49-7 (S)-N-tert-butoxycarbonyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine 
• 72155-45-4 Boc-L-phenylalaninal 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 319914-34-6 1-acetoxy-3-<<(1,1-dimethylethoxy)carbonyl>amino>-4-phenyl-2-butanone 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 193953-56-9 (4S,5S)-4-benzyl-5-benzyloxymethyl-1,3-oxazolidin-2-one 
• 1053517-88-6 (2S,3S)-3-Amino-1-benzyloxy-4-phenyl-butan-2-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 474022-71-4 (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol 

Downstream Products

• 149451-81-0 (2S,3S)-3-(tert-butoxycarbonyl)amino-4-phenyl-1-tosyloxy-2-butanol 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 388072-87-5 [(1S,2R)-1-benzyl-2-hydroxy-3-(3-methoxybenzylamino)propyl]carbamic acid tert-butyl ester 
• 388073-85-6 [(1S,2R)-1-benzyl-2-hydroxy-3-(1-methyl-1-phenylethylamino)propyl]carbamic acid tert-butyl ester 
• 1539276-53-3 biphenyl-3,5-dicarboxylic acid 5-({(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]propyl}amide) 3-dipropylamide 
• 1539276-52-2 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]propyl}-N',N'-dipropyl-5-pyrrolidin-1-ylisophthalamide 
• 1539276-51-1 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]-propyl}-5-cyclohexyl-N',N'-dipropylisophthalamide 
• 1539276-50-0 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]propyl}-5-piperidin-1-ylisophthalamide 
• 1539276-49-7 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]propyl}-3-piperidin-1-yl-5-(pyrrolidine-1-carbonyl)benzamide 
• 1539276-48-6 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)-1-methylethylamino]propyl}-5-piperidin-1-yl-N'-propylisophthalamide 
• 1539276-47-5 N-[(1S,2R)-1-benzyl-2-hydroxy-3-(3-methoxybenzylamino)propyl]-5-piperidin-1-yl-N',N'-dipropylisophthalamide 
• 1539276-46-4 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(3-methoxyphenyl)cyclopropylamino]propyl}-5-piperidin-1-yl-N',N'-dipropylisophthalamide 
• 1539276-45-3 N-[(1S,2R)-1-benzyl-2-hydroxy-3-(3-methoxybenzylamino)propyl]-5-(1,1-dioxo-[1,2]thiazinan-2-yl)-N',N'-dipropylisophthalamide 
• 1539276-44-2 N-{(1S,2R)-1-benzyl-2-hydroxy-3-[1-(5-methoxypyridin-3-yl)-1-methylethylamino]propyl}-5-piperidin-1-yl-N',N'-dipropylisophthalamide 

Relevant articles and documents

Peptidomimetic plasmepsin inhibitors with potent anti-malarial activity and selectivity against cathepsin D

Following up the open initiative of anti-malarial drug discovery, a GlaxoSmithKline (GSK) phenotypic screening hit was developed to generate hydroxyethylamine based plasmepsin (Plm) inhibitors exhibiting growth inhibition of the malaria parasite Plasmodium falciparum at nanomolar concentrations. Lead optimization studies were performed with the aim of improving Plm inhibition selectivity versus the related human aspartic protease cathepsin D (Cat D). Optimization studies were performed using Plm IV as a readily accessible model protein, the inhibition of which correlates with anti-malarial activity. Guided by sequence alignment of Plms and Cat D, selectivity-inducing structural motifs were modified in the S3 and S4 sub-pocket occupying substituents of the hydroxyethylamine inhibitors. This resulted in potent anti-malarials with an up to 50-fold Plm IV/Cat D selectivity factor. More detailed investigation of the mechanism of action of the selected compounds revealed that they inhibit maturation of the P. falciparum subtilisin-like protease SUB1, and also inhibit parasite egress from erythrocytes. Our results indicate that the anti-malarial activity of the compounds is linked to inhibition of the SUB1 maturase plasmepsin subtype Plm X.

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